Released in the U.S. on May 7, 1996, via Bulk Recordings, the debut album from Kool Keith as Dr. Octagon is one of the weirder masterpieces in the Hip-Hop canon. The Dr. Octagon persona first appeared on the Ultramagnetic MC's demo "Smoking Dust," and after recording two tracks ("Technical Difficulties" and "Dr. Octagon") with Kutmasta Kurt, the bizarre wordplay and surrealist approach of Dr. Octagon came into full form as Dan the Automator came onboard to produce a full-fledged album.

And what an album. Keith's legacy as rap's oddest oddball is largely cemented here. So without further ado, Stereo Williams and LeMayne James break down the weirdass genius of Dr. Octagonecologyst. 

The album lets you know from jump that this is going to be a strange trip; inviting you into the conceptualism of it all.  It set the gold mark for storytelling and themes. But, like, who puts porno clips on their album. On "3000," the unapologetic eccentricity is what gets your attention, but what keeps it is the craft. Dan the Automator is a superproducer when it comes to left-leaning, "alternative" rap classics; like the Pete Rock of oddballs.  

"I Got To Tell You" is a skit that sort of explains the character for you. In case you weren't already convinced that this was going to be a surreal trip. Here's an "ad' for Dr. Octagon. And "Earth People" is the perfect song for someone who's never heard this album before. References to "space doo-doo pistols' make it one of the album's definitive moments and it's so damn Kool Keith, with an ominous synth line that is fucking perfect. It sums up a lot about the album: murky, kinda dark, oddly funny. And the production on "No Awareness" is perfect here; this almost evokes a sorta 3 Feet High and Rising vibe with the intro, before Keith takes it into super strange territory. The whimsy disappears and that trademark murkiness comes in. It's one of the best songs on the album.   

"Technical Difficulties" is a great showcase if one ever had to explain to someone what stream-of-consciousness rhyming is: line like "Space connected while you listen to Keith Sweat" and "Zapp like Roger."LeMayne: Now this was my first intro to this album. He name-drops Jimmy Castor and Pepto Bismol in the same verse. What the fuck is there to not like? "General Hospital" is the kind of skit that the streaming era has all but marginalized. I know that for some people they became tedious, but on albums like this, you need them. The conceptualism is what drives the whole album and there are lots of albums where you need the skits tying themes together. This is one of those albums. 

"Blue Flowers" might be the best song here. DJ Qbert's scratching on the outro is one of the greatest on a surreal masterpiece. On "A Trip To the Gynecologist" I rarely, if ever, like to play the "how would this be received today" game. Keith is going for weirdness and creepiness-as-a-conceit, not endorsing creepiness as a lifestyle. It's all for the concept. And "Bear Witness" is one of the best DJ tracks of the 1990s; Qbert really is the third brain of the album. The chemistry these guys had when they were really clicking -- it's staggering.  

The title track is a theme song for a time-traveling gynecologist from outer space. There's always been some back-and-forth as to who produced what, but the soundscape used here is brilliant. It seems to set the stage for what Automator would do with Del years later.  And "Girl Let Me Touch You" is a love song - right? LOL It references STDs, cunnilingus, bondage and all types of other stuff. It's like a spoof of a love song. Even with the raunchy focus, it never feels all that sincere. It's still on some stream-of-consciousness shit, even if it's horny as hell. It sounds like the "Doctor" is a nymphomaniac, too.   

"I'm Destructive" is the most Ultramags sounding track here, like a throwback to Critical Beatdown. "Bash in your head with ten full cans of Campbell's soup/I'm on the roof, I'm not another pigeon out the chicken coop." This shit is perfect. It's followed by "Wild & Crazy," another Ultramagnetic MCs-sounding moment on the album. Right down to the "Ego Trippin'" sample/reference. This is definitely a callback to the legacy of the Ultramags. It still has the haziness of Dr. Octagon.

On "Waiting List" DJ Shadow does his thing, as the lyrics are brilliantly off-kilter. "Watching people vomit green, my potent, my list of pills/My office in Burbank, I hide the bodies in Beverly Hills/Seeking kibbles 'n bits, a girl with small tits/Talking to herself, her dog, and having rabid fits..." The imagery! The ever-lovin' imagery!

And "halfsharkalligatorhalfman" is a showcase for Mr. Gerbik, who is another weird character. "People think I'm mixed with shark, drinking gasoline." Lyrics like "In my raw world, orangutans dance for Thanksgiving/With skeleton bones and skunk tails is my mission..." linger long after the track is done. Quintessentially Keith.